Triethylsilane → 3-(6-fluoro-5-methylpyridin-2-yl)-5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridine

HRID 1775076Notes

Reaction equation

HRID 1775076 reaction equation
[F:1][C:2]1[N:7]=[C:6]([C:8]2[C:16]3[C:11](=[CH:12][N:13]=[C:14]([C:17]4[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=4)[CH:15]=3)[N:10](COCC[Si](C)(C)C)[N:9]=2)[CH:5]=[CH:4][C:3]=1[CH3:31].FC(F)(F)S(O)(=O)=O.C([SiH](CC)CC)C>FC(F)(F)C(O)=O.C(Cl)Cl>[F:1][C:2]1[N:7]=[C:6]([C:8]2[C:16]3[C:11](=[CH:12][N:13]=[C:14]([C:17]4[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=4)[CH:15]=3)[NH:10][N:9]=2)[CH:5]=[CH:4][C:3]=1[CH3:31]

Participants

6

Reactant 3

HCID 12052TriethylsilaneHCID 62406Trifluoromethanesulfonic acidHCID 712536643-(6-fluoro-5-methylpyridin-2-yl)-5-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridine

Product 1

HCID 712539543-(6-fluoro-5-methylpyridin-2-yl)-5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridineYield 11%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

3-(6-Fluoro-5-methylpyridin-2-yl)-5-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridine was dissolved in trifluoroacetic acid (5 mL) and methylene chloride (5 mL). To the solution was added trifluoromethanesulfonic acid (104.2 uL, 1.18 mmol) and triethylsilane (18.1 uL, 1.18 mmol). The resulting mixture was stirred overnight at room temperature. The mixture was then concentrated, and the residue was purified by reverse phase HPLC to afford 274 as an off-white solid (7.8 mg, 11%). 1H NMR (400 MHz, DMSO) δ 9.29-9.21 (m, 2H), 8.81 (s, 1H), 8.62 (dd, J=4.7, 1.4 Hz, 1H), 8.42 (dt, J=8.0, 1.9 Hz, 1H), 8.06 (dd, J=7.6, 1.6 Hz, 1H), 8.01-7.95 (m, 1H), 7.55 (dd, J=8.0, 4.8 Hz, 1H), 2.34 (s, 3H); ESI MS m/z=306.1 (M+1)

Workup

  1. concentrationThe mixture was then concentrated
  2. customthe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-ef37eafea32a469c930cc67a74e3876a
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

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